AustralieFrV1, PascalFrancis, Corpus, bibRecord, 001159

Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior

Identifieur interne : 001159 ( PascalFrancis/Corpus ); précédent : 001158; suivant : 001160

Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior

Auteurs : Pawel Gawrys ; Anna Zoltowska ; Malgorzata Zagorska ; Adam Pron

Source :

Electrochimica acta [ 0013-4686 ] ; 2011.

RBID : Pascal:12-0325093

Descripteurs français

Pascal (Inist)
- Copolymère alterné, Polymère électroactif, Imide copolymère, Semiconducteur, Synthèse chimique, Spectroélectrochimie, Thiophène dérivé copolymère, Spectrométrie UV visible, Propriété électrochimique, Voltammétrie cyclique, Semiconducteur organique, Polymère conducteur, Naphtalène-1,4,5,8-tétracarboximide dérivé, Benzo[lmn][3,8]phénanthroline-1,3,6,8-tétraone dérivé.

English descriptors

KwdEn :
- Alternating copolymer, Chemical synthesis, Conducting polymers, Cyclic voltammetry, Electroactive polymer, Electrochemical properties, Imide copolymer, Organic semiconductors, Semiconductor materials, Spectroelectrochemistry, Thiophene derivative copolymer, Ultraviolet visible spectrometry.

Abstract

Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-terthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.

Notice en format standard (ISO 2709)

Pour connaître la documentation sur le format Inist Standard.

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A14	`01`			`@1 Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3 @2 00 664 Warszawa @3 POL @Z 1 aut. @Z 2 aut. @Z 3 aut.`
A14	`02`			`@1 INAC/SPrAM, UMR 5819 CEA-CNRS-University J. Fourier-Grenoble 1, Laboratoire d'Electronique Moléculaire Organique et Hybride, 17 Rue des Martyrs @2 38054 Grenoble @3 FRA @Z 4 aut.`
A15	`01`			`@1 CNRS @2 Toulouse @3 FRA @Z 1 aut.`
A15	`02`			`@1 Monash University @2 Clayton, Vic. @3 AUS @Z 2 aut.`
A15	`03`			`@1 University of Houston @2 Houston, TX @3 USA @Z 3 aut.`
A15	`04`			`@1 LEPMI @2 Grenoble @3 FRA @Z 4 aut.`
A15	`05`			`@1 University of Palermo @3 ITA @Z 5 aut.`
A15	`06`			`@1 Lund University @3 SWE @Z 6 aut.`
A15	`07`			`@1 Eotvos Lorand University @2 Budapest @3 HUN @Z 7 aut.`
A15	`08`			`@1 CNRS @2 Nancy @3 FRA @Z 8 aut.`
A15	`09`			`@1 Wildau University @3 DEU @Z 9 aut.`
A15	`10`			`@1 Polish Academy of Sciences @2 Warsaw @3 POL @Z 10 aut.`
A15	`11`			`@1 Université de Strasbourg @3 FRA @Z 11 aut.`
A15	`12`			`@1 Nanyang Technological University @3 SGP @Z 12 aut.`
A15	`13`			`@1 Moscow State University @3 RUS @Z 13 aut.`
A15	`14`			`@1 Université Pierre et Marie Curie @2 Paris @3 FRA @Z 14 aut.`
A15	`15`			`@1 University of Münster @3 DEU @Z 15 aut.`
A18	`01`	`1`		`@1 International Society of Electrochemistry (ISE) @2 1004 Lausanne @3 CHE @9 org-cong.`
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C01	`01`		`ENG`	@0 Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-terthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.
C02	`01`	`X`		`@0 001D09D04D`
C03	`01`	`X`	`FRE`	`@0 Copolymère alterné @2 NK @5 01`
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C03	`01`	`X`	`SPA`	`@0 Copolímero alternado @2 NK @5 01`
C03	`02`	`X`	`FRE`	`@0 Polymère électroactif @5 02`
C03	`02`	`X`	`ENG`	`@0 Electroactive polymer @5 02`
C03	`02`	`X`	`SPA`	`@0 Polímero electroactivo @5 02`
C03	`03`	`X`	`FRE`	`@0 Imide copolymère @2 NK @5 03`
C03	`03`	`X`	`ENG`	`@0 Imide copolymer @2 NK @5 03`
C03	`03`	`X`	`SPA`	`@0 Imida copolímero @2 NK @5 03`
C03	`04`	`X`	`FRE`	`@0 Semiconducteur @5 04`
C03	`04`	`X`	`ENG`	`@0 Semiconductor materials @5 04`
C03	`04`	`X`	`SPA`	`@0 Semiconductor(material) @5 04`
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C03	`05`	`X`	`ENG`	`@0 Chemical synthesis @5 05`
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C03	`06`	`X`	`FRE`	`@0 Spectroélectrochimie @5 06`
C03	`06`	`X`	`ENG`	`@0 Spectroelectrochemistry @5 06`
C03	`06`	`X`	`SPA`	`@0 Espectroelectroquímica @5 06`
C03	`07`	`X`	`FRE`	`@0 Thiophène dérivé copolymère @2 NK @5 07`
C03	`07`	`X`	`ENG`	`@0 Thiophene derivative copolymer @2 NK @5 07`
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C03	`08`	`X`	`FRE`	`@0 Spectrométrie UV visible @5 08`
C03	`08`	`X`	`ENG`	`@0 Ultraviolet visible spectrometry @5 08`
C03	`08`	`X`	`SPA`	`@0 Espectrometría UV visible @5 08`
C03	`09`	`X`	`FRE`	`@0 Propriété électrochimique @5 09`
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N21				`@1 247`

A30	`01`	`1`	`ENG`	`@1 International Society of Electrochemistry (ISE) Meeting @2 61 @3 Nice FRA @4 2010-09-26`

Format Inist (serveur)

NO :	PASCAL 12-0325093 INIST
ET :	Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior
AU :	GAWRYS (Pawel); ZOLTOWSKA (Anna); ZAGORSKA (Malgorzata); PRON (Adam); BERGEL (A.); BOND (A. M.); BRANKOVIC (S.); BULTEL (Y.); DI QUARTO (F.); GORTON (L.); INZELT (G.); LAPICQUE (F.); LISDAT (F.); OPALLO (M.); SAVINOVA (E. R.); TOH (C.S.); TSIRLINA (G. A.); VIVIER (V.); WINTER (M.)
AF :	Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3/00 664 Warszawa/Pologne (1 aut., 2 aut., 3 aut.); INAC/SPrAM, UMR 5819 CEA-CNRS-University J. Fourier-Grenoble 1, Laboratoire d'Electronique Moléculaire Organique et Hybride, 17 Rue des Martyrs/38054 Grenoble/France (4 aut.); CNRS/Toulouse/France (1 aut.); Monash University/Clayton, Vic./Australie (2 aut.); University of Houston/Houston, TX/Etats-Unis (3 aut.); LEPMI/Grenoble/France (4 aut.); University of Palermo/Italie (5 aut.); Lund University/Suède (6 aut.); Eotvos Lorand University/Budapest/Hongrie (7 aut.); CNRS/Nancy/France (8 aut.); Wildau University/Allemagne (9 aut.); Polish Academy of Sciences/Warsaw/Pologne (10 aut.); Université de Strasbourg/France (11 aut.); Nanyang Technological University/Singapour (12 aut.); Moscow State University/Russie (13 aut.); Université Pierre et Marie Curie/Paris/France (14 aut.); University of Münster/Allemagne (15 aut.)
DT :	Publication en série; Congrès; Niveau analytique
SO :	Electrochimica acta; ISSN 0013-4686; Coden ELCAAV; Royaume-Uni; Da. 2011; Vol. 56; No. 28; Pp. 10464-10472; Bibl. 33 ref.
LA :	Anglais
EA :	Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-te rthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N, N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-p henylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1 ,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.
CC :	001D09D04D
FD :	Copolymère alterné; Polymère électroactif; Imide copolymère; Semiconducteur; Synthèse chimique; Spectroélectrochimie; Thiophène dérivé copolymère; Spectrométrie UV visible; Propriété électrochimique; Voltammétrie cyclique; Semiconducteur organique; Polymère conducteur; Naphtalène-1,4,5,8-tétracarboximide dérivé; Benzo[lmn][3,8]phénanthroline-1,3,6,8-tétraone dérivé
ED :	Alternating copolymer; Electroactive polymer; Imide copolymer; Semiconductor materials; Chemical synthesis; Spectroelectrochemistry; Thiophene derivative copolymer; Ultraviolet visible spectrometry; Electrochemical properties; Cyclic voltammetry; Organic semiconductors; Conducting polymers
SD :	Copolímero alternado; Polímero electroactivo; Imida copolímero; Semiconductor(material); Síntesis química; Espectroelectroquímica; Tiofeno derivado copolímero; Espectrometría UV visible; Propiedad electroquímica; Voltametría cíclica
LO :	INIST-1516.354000505919820210
ID :	12-0325093

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Pascal:12-0325093

Le document en format XML

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<front><div type="abstract" xml:lang="en">Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-terthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.</div>
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<fA08 i1="01" i2="1" l="ENG"><s1>Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior</s1>
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<fA15 i1="05"><s1>University of Palermo</s1>
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<fA15 i1="06"><s1>Lund University</s1>
<s3>SWE</s3>
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<fA15 i1="07"><s1>Eotvos Lorand University</s1>
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<fA15 i1="10"><s1>Polish Academy of Sciences</s1>
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<fA15 i1="13"><s1>Moscow State University</s1>
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<fA15 i1="15"><s1>University of Münster</s1>
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<fA18 i1="01" i2="1"><s1>International Society of Electrochemistry (ISE)</s1>
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<fC01 i1="01" l="ENG"><s0>Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-terthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.</s0>
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<s5>10</s5>
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<fC03 i1="14" i2="X" l="FRE"><s0>Benzo[lmn][3,8]phénanthroline-1,3,6,8-tétraone dérivé</s0>
<s4>INC</s4>
<s5>91</s5>
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<fN21><s1>247</s1>
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<ET>Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior</ET>
<AU>GAWRYS (Pawel); ZOLTOWSKA (Anna); ZAGORSKA (Malgorzata); PRON (Adam); BERGEL (A.); BOND (A. M.); BRANKOVIC (S.); BULTEL (Y.); DI QUARTO (F.); GORTON (L.); INZELT (G.); LAPICQUE (F.); LISDAT (F.); OPALLO (M.); SAVINOVA (E. R.); TOH (C.S.); TSIRLINA (G. A.); VIVIER (V.); WINTER (M.)</AU>
<AF>Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3/00 664 Warszawa/Pologne (1 aut., 2 aut., 3 aut.); INAC/SPrAM, UMR 5819 CEA-CNRS-University J. Fourier-Grenoble 1, Laboratoire d'Electronique Moléculaire Organique et Hybride, 17 Rue des Martyrs/38054 Grenoble/France (4 aut.); CNRS/Toulouse/France (1 aut.); Monash University/Clayton, Vic./Australie (2 aut.); University of Houston/Houston, TX/Etats-Unis (3 aut.); LEPMI/Grenoble/France (4 aut.); University of Palermo/Italie (5 aut.); Lund University/Suède (6 aut.); Eotvos Lorand University/Budapest/Hongrie (7 aut.); CNRS/Nancy/France (8 aut.); Wildau University/Allemagne (9 aut.); Polish Academy of Sciences/Warsaw/Pologne (10 aut.); Université de Strasbourg/France (11 aut.); Nanyang Technological University/Singapour (12 aut.); Moscow State University/Russie (13 aut.); Université Pierre et Marie Curie/Paris/France (14 aut.); University of Münster/Allemagne (15 aut.)</AF>
<DT>Publication en série; Congrès; Niveau analytique</DT>
<SO>Electrochimica acta; ISSN 0013-4686; Coden ELCAAV; Royaume-Uni; Da. 2011; Vol. 56; No. 28; Pp. 10464-10472; Bibl. 33 ref.</SO>
<LA>Anglais</LA>
<EA>Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-te rthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N, N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-p henylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1 ,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.</EA>
<CC>001D09D04D</CC>
<FD>Copolymère alterné; Polymère électroactif; Imide copolymère; Semiconducteur; Synthèse chimique; Spectroélectrochimie; Thiophène dérivé copolymère; Spectrométrie UV visible; Propriété électrochimique; Voltammétrie cyclique; Semiconducteur organique; Polymère conducteur; Naphtalène-1,4,5,8-tétracarboximide dérivé; Benzo[lmn][3,8]phénanthroline-1,3,6,8-tétraone dérivé</FD>
<ED>Alternating copolymer; Electroactive polymer; Imide copolymer; Semiconductor materials; Chemical synthesis; Spectroelectrochemistry; Thiophene derivative copolymer; Ultraviolet visible spectrometry; Electrochemical properties; Cyclic voltammetry; Organic semiconductors; Conducting polymers</ED>
<SD>Copolímero alternado; Polímero electroactivo; Imida copolímero; Semiconductor(material); Síntesis química; Espectroelectroquímica; Tiofeno derivado copolímero; Espectrometría UV visible; Propiedad electroquímica; Voltametría cíclica</SD>
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Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior

Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior

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